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Adii Pienaar

Now working on Receiptful. Co-Founder & ex-CEO of WooThemes. Author of Brandiing. New Dad. Ex-Rockstar.


“How much I missed, simply because I was afraid of missing it.” ~ Paulo Coelho (Tweet This)

Opportunities are oddly binary in the way they always seem to work.

An opportunity presents itself. Or it doesn't.

You take an opportunity. Or you pass on it.

You wish you had an opportunity. Or you curse the fact that you have too many and don't know which one to take.

Thinking about this, I've been wondering whether opportunities actually has a middle ground somewhere and whether that space contains a sweet spot of sorts.

For a very long time, I defined an entrepreneur as:

  • Someone who can spot an opportunity; and
  • Take action to benefit from an opportunity.

Today, I've not strayed from this definition and whilst my definition of entrepreneurship has evolved slightly over time, opportunities (and what one does with them) is still a central part of that definition.

Looking at my own trajectory as an entrepreneur, spotting a gap and taking an action was a major part of why WooThemes ever got created. If I think about those early days, I'm often drawn to this quote from Thomas Edison:

"Opportunity is missed by most people because it is dressed in overalls and looks like work."

This seems particularly apt at the time. The opportunity that spawned WooThemes didn't necessarily seem as such at the time; instead it was just something that I could work on (and was crazy enough to quit my job in the pursuit thereof).

Ever since I had my first real start based on spotting and exploiting an opportunity, I've forced myself to get even better at opportunities.

I use "opportunities" as an almost-verb in that previous sentence, because that's how it sometimes feels: it doesn't make sense, I don't know what I'm really doing (i.e. it's not a science), but I'm still doing it.

This has been a great mindset to have as an entrepreneur, but even at the best of times it's been like having an angel on one and a devil on the other shoulder; both offering contradicting thoughts and advice at every fork in the road.

On the good end, it helped me create and steer WooThemes to great success. But on the other end, it has also left various failures in its wake, because what seemed like a good opportunity either wasn't an opportunity at all or it was just a shitty one.

So I've had to get better at thinking about and taking opportunities. This is how I've done it:

1. Explore Aggressively, Execute Cautiously

I'm a dreamer and a big part of what makes me good at entrepreneurship is the ability to see a better tomorrow. This has meant that I'm always knocking on doors or opening them to see what hides behind. I do this religiously, aggressively and with a beyond-average amount of persistence.

Milton Berle says it best:

“If opportunity doesn't knock, build a door.”

But there's no balance in this and an exclusively forward-facing entrepreneur leaves blind spots in his peripheral. (Tweet This)

Blind spots that leads to bad decisions, failures and lost time (or money).

So I've adapted my approach to play to my strength (of seeking opportunity), but I'm incredibly cautious when it comes to actually executing on an opportunity. Sometimes I'll spent weeks researching an opportunity, only to walk away eventually; not because it's a bad opportunity, but because it's not an opportunity for me.

2. Accepting the nature of opportunities

Coming back to the seemingly binary nature of opportunities, I've forced myself to accept this status quo and the probabilities attached to it.

One of these inherent flaws of opportunities is that by taking one opportunity today, you'll probably have to sacrifice two tomorrow (because time, energy and / or money is finite). That means that there's no way to know whether there'll be a better (or worse) opportunity that comes your way tomorrow.

So the only way to make a decision is to make it based on the data you have today. If the opportunity feels right and makes sense today, just do it.

The other thing about opportunities is that it's very much like standing on the edge of a forest.

On the edge, you can only see these huge trees, which presents a good and ominous opportunity. Before breaching that edge and getting stuck into the routes within the forest, there's no way for you to know what you'll find.

The trees might look promising on the edge, but slightly beyond this edge, you might realize that the forest simply isn't that great.

This is natural and you can't control this part of opportunities. You can however control your actions (even if it is a reaction) in these situations.

3. No Regrets

If you're prone to regret, you'll have to learn to shake that. Regret is just baggage that clouds your future judgement.

I struggle with this, but I mostly avoid feeling any regret about either the opportunities I took or the one's I missed.

"Failure is simply the opportunity to begin again, this time more intelligently." ~ Henry Ford

My father-in-law always told my wife (when she was younger) to never chase after a boy or a bus, because the next one is just around the corner. This is again part of the natural anatomy of an opportunity and it's something worth accepting (regardless of your comprehension thereof).

Proactive acceptance will make you less prone to the possibility of regret.

And also know that regret works both ways in any decision. Take the road less traveled and you might end up regretting the loneliness thereof. Or take the mainstream approach and you'll regret "me-too"-ing.

4. Opportunities have different life cycles

Many of the greatest opportunities presents itself within an ephermal moment and the trick with these is to take action as quickly as possible, because the proverbial window of opportunity can actually pass.

But on the other side, some opportunities actually requires time to percolate and presents you with weeks and months to figure it out. Sometimes the very nature of rushing into these opportunities will slow you down.

The trick here is to recognize which is which, because the natural life cycle of an opportunity should influence your decision-making.

I'm a very impulsive person by nature and I've made some of my best decisions in life based on my intuition whilst on the fly. But I've also pursued opportunities in this way, where I should've instead not rushed. As you can imagine, those decisions lead to failure and a loss of sorts.

5. Consider The Context

No opportunity is ever isolated and only about the opportunity itself. In fact, taking just the timing of when an opportunity is uncovered, should already form a great part of the context that surrounds any decision you could / should make.

I've been in countless situations where the opportunity (in isolation) makes so much sense, but either my timing or current position simply didn't make the pursuit thereof ideal or efficient.

Take for example my pursuit of PublicBeta; great idea, but the timing ended up being wrong. If I had considered the greater context before I took the plunge with PublicBeta, I might've made a different decision with regards to the taking the opportunity.

Consider all of the facts that comes as part-and-parcel with any opportunity and consider the impact thereof on the holistic version of you / your life. What does it mean for you professionally or relating to your ambition / purpose? What's the impact on family, friends and other people that are important to you? And ultimately how could this opportunity affect you, as an individual?

Opportunities are anything but an exact science. (Tweet This)

I sometimes think that the only reason why opportunities are so awesome is that they are inherently imperfect.

To that extent, I've come to think about opportunities in a way that allows me to diversify my interests: How can I take - or not take - multiple opportunities to increase my rate of return?

Opportunities are about optimizing on this mindset; not going all-in. (Tweet This)

“The Chinese use two brush strokes to write the word 'crisis.' One brush stroke stands for danger; the other for opportunity. In a crisis, be aware of the danger - but recognize the opportunity.”

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